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Synthesis 2005(16): 2758-2764  
DOI: 10.1055/s-2005-872095
PAPER
© Georg Thieme Verlag Stuttgart · New York

Ring Transformations of Pentose Glycals with Push-Pull Butadiene Functionality

Ahmed Baria, Selena Milicevica, Holger Feista , Dirk Michalikb, Manfred Michalik*b, Klaus Peseke*a
a Universität Rostock, Institut für Chemie, Albert-Einstein-Str. 3a, 18051 Rostock, Germany
Fax: +49(381)4986412; e-Mail: klaus.peseke@uni-rostock.de;
b Leibniz-Institut für Organische Katalyse, Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
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Publication History

Received 17 March 2005
Publication Date:
22 July 2005 (online)

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Abstract

2-Formyl-d-xylal (1a) and 2-formyl-l-arabinal (1b) were reacted with alkyl cyanoacetates to furnish the 1,5-anhydro-3,4-di-O-benzyl-2-[(E)-2-cyano-2-alkoxycarbonylvinyl]-2-deoxy-d(l)-hex-1-enitols 2a and 2b, respectively. Treatment of 2a, 2b with aromatic amines afforded the 1-aryl-5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydro-2-oxopyridine-3-carbonitriles 3a-c. Ring transformation of 1a, 1b with N-substituted oxobutyramides, dialkyl 3-oxopentanedioate and benzimidazol-2-ylacetonitrile yielded the 3-acetyl-1-aryl-5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-1,2-dihydropyridin-2-ones 6a-d, alkyl 5-[1,2-bis(benzyloxy)-3-hydroxypropyl]-2-hydroxyisophthalates 8a-d and 2-[1,2-bis(benzyloxy)-3-hydroxypropyl]benzo[4,5]imidazo-[1,2-a]-pyridine-4-carbonitriles 11a, 11b, respectively.

Key words

carbohydrates - heterocycles - nucleosides - ring opening - ring closure